Nobody likes being second guessed. So with the GM meetings beginning a few hours after this piece is posted, and the free agent frenzy due to start in a week, it's time to do some first-guessing.

First of all, there is one large caveat to my off-season plan. Given my own way, I would have started in May. Back then, I was banging the drum for Pods and Erstad to be released (in one form or another), Dye to be traded, and Buehrle re-signed. The last of which seemed a bit of pipe dream at the time, but 6 weeks later became reality.

The Pierzynski and Dye extensions have dictated the Sox moves in '08 (and even '09). They've backed themselves into a position where they must spend (ridiculous amounts of) money through the free agent market in order to put a competitive team on the field the next two seasons.

Back in May, I said the Sox couldn't stand a full-fledged rebuilding effort, and the same still holds true today. So while I might want the Sox to get younger, and fast, first they may have to get older.

As we've written a number of times over the last two seasons, the Sox minor league system is in a sorry state. There are a precious few impact players in the entire system, and only one can be (realistically) projected to make the '09 team. This lack of organizational talent has cost a number of people their jobs, and further forces the hand of the front office.

Doing this exercise, I've come around to the notion that the White Sox will have to buy time as much as talent on the open market. My mid-season plan to dump Dye and others for youth would have dumped payroll and made the Sox more financially nimble, but the reality is that they still would have been bad in '08, and '09, and probably '10 too. If the Sox have the budget to field competitive teams between now and '10, they should do so as long as they don't sacrifice the key minor league talent that will push them to their next playoff contender in '11.

For the purposes of this post, I'm going to use a budget of about $115M (I could see them going as high as $125M under the right circumstances). There's no way to know exactly what the White Sox '08 budget will be, but attendance remained strong, which for the White Sox almost always correlates to money spent the following season. And there have been whispers of MLBAM, mainly the MLB.TV revenue, seeing another large increase this season, which should make all teams flush with cash and push free agent salaries even higher than last year.

The Sox already have $90M committed to 12 players in '08, and that's without a 3B (Crede's arbitration award not included), a SS (Uribe's buyout exercised), or a CFer (Erstad has been bought out). Filling just those 3 holes on the free agent market would push them to the $115M very quickly. $90M + $13M (Rowand w/ discount) + $7M (Eckstein) + $5-10M (for a LFer in a Crede trade) puts the Sox at $115-120M even before adding in the low-salary guys. As such, I forsee the Sox needing to trade off some salary.

Crede and one of Contreras/Garland are still the main trade pieces, but instead of flipping them for young, multi-tooled players they should be turned into veterans who provide a better fit to the club and/or have the chance to be Type A free agents in '08. Crede has zero chance of becoming a Type A thanks to his '07 and Garland's win total in '07 also limits his compensation value. If these two could be flipped for departing probable Type A free agents, the Sox could quickly infuse high quality new talent into the organization while remaining competitive in the interim.

If both Burrell and Furcal have good seasons and are offered arbitration following the season, the Sox could be looking at 5 picks in the first 60. To put that in perspective, in the last three drafts the Sox have had a total of 6 picks in the top 100. Such an infusion of talent can not be discounted. (Fields and Gio are both products of the 2004 draft which saw the Sox take 5 of the first 59 players drafted.) The teams which have used this strategy most effectively recently are the Yankees and Red Sox, who have combined to take Jacoby Ellsbury, Craig Hansen, Clay Buchholz, Michael Bowden, Ian Kennedy, and Joba Chamberlain in the first or supplemental rounds since '05.

In this scenario, I would look to add Mike Cameron, who remains a plus defensive CFer and one of the best baserunners in the game, won't need a long-term commitment, and might come at a bit of a discount thanks to his impending 25-game suspension. I would look to avoid the two Type A CFers (Rowand, Hunter), signing whom will cost the Sox their '08 2nd rounder. I wouldn't be against giving Furcal an extension, but would prefer him to turn into draft picks, and revisit this scenario next season.

In the bullpen, the Sox need one "veteran arm," and I'm going to suggest a familiar one; Kerry Wood. Because he was hurt again for the first half of last season, he might not get the multi-year deal that he covets. I doubt he'd sign anywhere other than the Cubs on a 1-year deal, but 2 years might not be a bad investment. I wouldn't spend more than $8M over the 2-year contract, and am unsure about whether he could receive more. (This one's just thrown at the wall. I can't accurately predict reliever value.)

There are glaring weaknesses to this proposed club, but I'm just looking to be competitive (80-85 wins) in '08, not win a title. The Sox would need every star in the sky to align to achieve that goal.

I'm not going to go on a rant when the Sox don't follow the South Side Sox Officially Sanctioned Plan™ to the letter. I know they won't. I'll be looking for them to follow the following edicts:

• No contracts longer than 2 years (I could be persuaded to 3) to 30-and-over players.
• Do not sign any Type A Free Agents not named A-Rod.
• Practice restraint on the open market.
• Hold onto the following 3 minor leaguers in any trade (in order): DLS, Gio, Carter.

Salary charts with projected probable rosters after the jump

Current Roster obligations (no Crede)

Pos   Name                   2008     2009     2010    2011
P     Buehrle, Mark        $14.00   $14.00   $14.00  $14.00
P     Contreras, Jose      $10.00   $10.00
OF    Dye, Jermaine         $9.50   $11.50    $1.00
OF    Erstad, Darin         $0.25
P     Garland, Jon         $12.00
C     Hall, Toby            $1.75    $0.15* 
1B    Konerko, Paul        $12.00   $12.00   $12.00
P     MacDougal, Mike       $1.95    $2.65    $0.35*
UTL   Ozuna, Pablo          $1.05    $0.20*  
C     Pierzynski, A.J.      $5.85    $6.25    $6.25
1B    Thome, Jim           $14.00    $3.00
P     Thornton, Matt        $0.875   $1.325   $0.25*
SS    Uribe, Juan           $0.30
P     Vazquez, Javier      $11.50   $11.50   $11.50 
============================================================
                           $95.025  $72.575  $45.35   $14.00
============================================================
      Cash (Thome)         ($5.00)
============================================================
                           $90.025  $72.575  $45.35   $14.00

South Side Sox Officailly Sanctioned Off-Season Plan

Pos   Name                   2008     2009     2010    2011
P     Buehrle, Mark        $14.00   $14.00   $14.00  $14.00
OF    Burrell, Pat         $14.00
P     Contreras, Jose      $10.00   $10.00
OF    Cameron, Mike        $11.50   $11.50
OF    Dye, Jermaine         $9.50   $11.50    $1.00
OF    Erstad, Darin         $0.25
SS    Furcal, Rafael       $13.00
C     Hall, Toby            $1.75    $0.15* 
1B    Konerko, Paul        $12.00   $12.00   $12.00
P     MacDougal, Mike       $1.95    $2.65    $0.35*
UTL   Ozuna, Pablo          $1.05    $0.20*  
C     Pierzynski, A.J.      $5.85    $6.25    $6.25
1B    Thome, Jim           $14.00    $3.00
P     Thornton, Matt        $0.875   $1.325   $0.25*
SS    Uribe, Juan           $0.30
P     Vazquez, Javier      $11.50   $11.50   $11.50 
============================================================
                          $121.525  $84.075  $45.35   $14.00
============================================================
      Cash (Thome)         ($5.00)
      Cash (Burrell)       ($4.00)
      Cash (Furcal)        ($3.00)
============================================================
                          $109.525  $84.075  $45.35   $14.00

Iceberg, what iceberg?

Pos   Name                   2008     2009     2010    2011
P     Buehrle, Mark        $14.00   $14.00   $14.00  $14.00
P     Contreras, Jose      $10.00   $10.00
OF    Dye, Jermaine         $9.50   $11.50    $1.00
OF    Damon, Johnny        $13.00   $13.00
SS    Eckstein, David       $6.00    $7.00    $8.00
OF    Erstad, Darin         $0.25
P     Garland, Jon         $12.00
C     Hall, Toby            $1.75    $0.15* 
1B    Konerko, Paul        $12.00   $12.00   $12.00
P     MacDougal, Mike       $1.95    $2.65    $0.35*
UTL   Ozuna, Pablo          $1.05    $0.20*  
C     Pierzynski, A.J.      $5.85    $6.25    $6.25
OF    Rowand, Aaron        $13.00   $13.00   $14.00   $14.00
1B    Thome, Jim           $14.00    $3.00
P     Thornton, Matt        $0.875   $1.325   $0.25*
SS    Uribe, Juan           $0.30
P     Vazquez, Javier      $11.50   $11.50   $11.50 
============================================================
                          $127.025  105.575  $67.35   $28.00
============================================================
      Cash (Thome)         ($5.00)
      Cash (Damon)         ($3.00)   (3.00)
============================================================
                          $119.025  102.575  $67.35   $28.00